Oakland Vacations from $202
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Save 100% on your flight
Price was $332, price is now $202 per person
$202
per person
Jan 29 - Feb 1
found 23 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
Their breakfast deal was a wonderful meal at their in house restaurant.
Reviewed on Nov 7, 2025
Hilton Garden Inn Pittsburgh Downtown
Downtown Pittsburgh
Save 100% on your flight
Price was $552, price is now $353 per person
$353
per person
Jan 29 - Feb 1
found 23 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
9/10 Wonderful! (1,151 reviews)
This hotel is great. Great location to our event. Our room was clean and comfortable with all the amenities that you could ask for. Hotel also has a great restaurant attached which was so convenient as we had a dinner and a breakfast. Staff very friendly and accommodating as well. Will definitely stay again.
Reviewed on Nov 29, 2025
Kimpton Hotel Monaco Pittsburgh by IHG
Downtown Pittsburgh
Save 100% on your flight
Price was $453, price is now $292 per person
$292
per person
Jan 29 - Feb 1
found 23 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,253 reviews)
Great hotel, excellent location.
Reviewed on Nov 25, 2025
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Save 100% on your flight
Price was $552, price is now $364 per person
$364
per person
Jan 29 - Feb 1
found 23 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Large, comfortable hotel that is conveniently located downtown and next door to the convention center.
Reviewed on Nov 29, 2025
Fairmont Pittsburgh
Downtown Pittsburgh
Save 100% on your flight
Price was $556, price is now $375 per person
$375
per person
Jan 29 - Feb 1
found 23 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8.8/10 Excellent! (1,002 reviews)
Staff and location of the hotel
Reviewed on Nov 26, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $119 total per night from Dec 21 to Dec 22
$119 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (520 reviews)
Nice. Tv remote did not work, a fail there. They refused to reimburse for that. Fail. I adked for room service. They agreed but never showed up. Otherwise I loved the pool.
Reviewed on Nov 27, 2025
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$99 nightly
The price is $113 total per night from Dec 7 to Dec 8
$113 total
Dec 7 - Dec 8
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
The breakfast was very good. It was not free, however very affordable. Restaurant staff was kind.
Reviewed on Nov 14, 2025
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $214 total per night from Dec 18 to Dec 19
$214 total
Dec 18 - Dec 19
Total with taxes and fees
9.2/10 Wonderful! (713 reviews)
.
Reviewed on Nov 28, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$72
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
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- University of Pittsburgh
- University of Pittsburgh Medical Center
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- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
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- Carnegie Mellon University
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- Market Square
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- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.